US4647389A - Anti-friction additives for lubricating oils - Google Patents
Anti-friction additives for lubricating oils Download PDFInfo
- Publication number
- US4647389A US4647389A US06/766,469 US76646985A US4647389A US 4647389 A US4647389 A US 4647389A US 76646985 A US76646985 A US 76646985A US 4647389 A US4647389 A US 4647389A
- Authority
- US
- United States
- Prior art keywords
- lubricating oil
- oil composition
- polyamine
- group
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/251—Alcohol fueled engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/28—Rotary engines
Definitions
- This invention relates to lubricating oils. More particularly, it relates to lubricating oil compositions containing an additive which imparts improvement in anti-friction and other lubrication properties.
- lubricating oil compositions contain a wide range of additives including those which possess anti-wear properties, anti-friction properties, anti-oxidant properties, and the like.
- additives including those which possess anti-wear properties, anti-friction properties, anti-oxidant properties, and the like.
- Those skilled in the art of lubricating oil additives are continuously seeking additives which may improve these properties without detrimental effect on other properties and which are inexpensive.
- the additive will have to be soluble and/or stabily dispersable is such oil compositions.
- oil-soluble it is meant that the subject compositions are soluble to an extent which permits the formed solution to exhibit one or more of the desired properties; e.g., anti-friction and anti-wear.
- stabily dispersable the compositions are capable of being suspended in the lubricating oil composition in an amount sufficient to allow the oil to possess one or more of the desired properties imparted to it by the suspended composition.
- the suspension of the composition can be achieved in various conventional ways such as by physical agitation and by the use of conventional dispersants.
- the lubricating oil composition comprises (i) a major portion of a lubricating oil; and (ii) a minor effective portion of, as an additive, a product prepared by reacting a natural oil with a (C 2 -C 10 ) hydroxy acid and a polyamine.
- the additive product may be represented by Formula I ##STR1## where R is a (C 7 -C 29 ) alkyl group; R 1 is a (C 1 -C 10 ) alkylene group; R 2 is a (C 1 -C 10 ) alkylene group which is not necessarily the same in each repeating bivalent radical; R 3 is a (C 2 -C 10 ) hydroxy acyl group having (1-9) hydroxyl groups, and/or the ##STR2## radical, and/or hydrogen with at least one R 3 group being a (C 2 -C 10 ) hydroxy acyl group or hydrogen in the repeating bivalent radicals; and n is an integer of 1 to 6.
- the lubricating oil additive which may be employed in the practice of this invention may have the formula I ##STR3## where R is a (C 7 -C 29 ) alkyl group; R 1 is a (C 1 -C 10 ) alkylene group; R 2 is a (C 1 -C 10 ) alkylene group which is not necessarily the same in each repeating bivalent radical; R 3 is a (C 2 -C 10 ) hydroxy acyl group having (1-9) hydroxyl groups, and/or the ##STR4## radical, and/or hydrogen with at least one R 3 group being a (C 2 -C 10 ) hydroxy acyl group or hydrogen in the repeating bivalent radicals; and n is an integer of 1 to 6.
- the fatty acid moiety may be characterized by the formula RCO--.
- Typical fatty acids may include those listed below in Table I.
- the preferred fatty acid is lauric acid.
- R may be a hydrocarbon group selected from the group consisting of alkyl, alkenyl, and alkynyl. When R is alkyl, it may typically be octyl, decyl, octadecyl, etc.
- the preferred R groups may be a C 8 -C 30 alkyl, more preferably a C 10 -C 20 alkyl, and most preferably a C 12 alkyl group.
- the fatty acid moiety may be derived from various commercially available fats and natural oils typified by those set forth below in Table II.
- the preferred natural oil is coconut oil which typically contains residues listed below in Table III.
- the C 2 -C 10 hydroxy acids used in the present preparation may include glycolic acid, lactic acid, hydracrylic acid, dihydroxyacids such as glyceric acid and poly hydroxyacids such as tri-(hydroxymethyl)acetic acid.
- the preferred acids are those having from 1 to 4 carbon atoms.
- the polyamine which may be used according to the present invention is selected from the group including diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), N,N'-bis-(3-aminopropyl)ethylene diamine (BAPEDA), and bis-(1,3-propylene)triamine.
- DETA diethylenetriamine
- TETA triethylenetetramine
- TEPA tetraethylenepentamine
- BAPEDA N,N'-bis-(3-aminopropyl)ethylene diamine
- bis-(1,3-propylene)triamine bis-(1,3-propylene)triamine.
- the reaction involves the interaction in between a natural oil such as coconut oil, a (C 2 -C 10 ) hydroxy acid such as glycolic acid and a polyamine such as diethylenetriamine (DETA).
- a natural oil such as coconut oil
- a (C 2 -C 10 ) hydroxy acid such as glycolic acid
- a polyamine such as diethylenetriamine (DETA).
- the reactants are provided in a molar ratio of natural oil to polyamine ranging from about 2:1 to about 10:1, and a molar ratio of hydroxy acid to polyamine ranging from about 0:1 to about 6:1.
- the additives may be added to a major portion of a hydrocarbon lubricating oil as a minor effective portion of preferably from about 0.05 to about 10.0 wt.%, and more preferably from about 0.20 to about 1.0 wt.%.
- the anti-friction additive may be prepared by the reaction of a natural oil, such as coconut oil and a polyamine, such as diethylenetriamine, which produces a product having the formula II ##STR5## where R is a (C 7 -C 29 ) straight chain alkyl group of a fatty acid.
- the natural oils listed in Table II above as well as amines such as DETA, TETA, TEPA, BAPEDA, and bis-(1,3 propylene) triamine may be used in the preparation of the additive represented above by formula II.
- the reactants are reacted under the same conditions and in the same molar ratios as used in preparing the additives represented by formula I.
- hydroxyacylated fatty acid amides of a polyamine can be combined with derivatives to form a variety of concentrates with the deliverants being substantially inert.
- the solvent, the diluent or the like is added to the compound of the subject invention, the properties of the same are not materially interfered with in such areas as compound preparation, storage, blending, and/or functioning in the context of its intended use.
- compositions of the subject invention can be employed in a variety of lubricants based on diverse oils of lubricating viscosity, including natural and synthetic lubricating oils and mixtures thereof.
- lubricants include crankcase lubricating oil for spark-ignited and compression-ignited internal combustion engines, including automobile and truck engines; two cylinder engines; aviation piston engines; marine and railroad diesel engines, and the like. They can also be used in gas engines, stationary power engines, and turbines and the like.
- Automatic transmission fluids, transaxle fluids, lubricant metal working lubricants, hydraulic fluids, and other lubricating oil and grease compositions can also benefit from the incorporation therein of the composition of the present invention.
- the polar part of the composition is adsorbed onto the metal surface to form a strongly bonded layer.
- the fatty alkyl groups attached to the lower polar portion of the composition extend out from the surface.
- the metal parts are in motion, the fatty alkyl groups reduce the degree of contact between the asperities of the parts, therefore, friction is correspondingly reduced.
- the metal parts are worn out less rapidly than if the hydroxyacylated fatty acid amide was not present in a contacting lubricating oil composition. Equally, as important, a fuel savings is realized and less fuel is required in any given circumstance as the amount of energy expended in overcoming frictional resistance is lessened.
- the lubricating oils which may be employed in the practice of the process of this invention may include a wide variety of hydrocarbon or synthetic lubricating oils used for example in automotive, aircraft, railroad, diesel, marine, tractor lubricating service for heavy duty or light duty, for winter or summer operations.
- lubricating compositions containing effective amounts of the present additives may be characterized by anti-wear and anti-friction properties.
- the low cost of the additives makes it possible in many instances to attain results comparable to prior art commercial friction modifiers but at a lower cost.
- the anti-wear properties of lubricating compositions containing the additives of this invention may show improved results when tested by the Four Ball Wear Test described below.
- the Four Ball Wear Test is carried out by securely clamping three highly polished steel balls (each 0.5 inch in diameter) in a test cup in an equilateral triangle in a horizontal plane.
- the fourth highly polished steel ball, resting on the three lower balls to form a tetrahedron, is held in a chuck.
- a weight lever arm system applies weight to the test cup, and this load holds the balls together.
- the speed of rotation is 1800 rpm; the load is 40 kilograms.
- the assembly is submerged in the liquid to be tested.
- the test is carried out at 200° F. for 60 minutes.
- the friction of the upper ball rotating in relation to the lower balls produces a wear-scar the diameter of which (i.e. the depth along a diameter of the ball) is measured.
- the average of the wear on the three lower balls is the rating assigned (in millimeters).
- the anti-friction properties of the additives of this invention may be equal to the "good reference” when tested in the Small Engine Friction Test (SEFT) described below.
- SEFT Small Engine Friction Test
- the Small Engine Friction Test uses a single cylinder, air-cooled, 6-horsepower engine driven by an electric motor.
- the engine has a cast-iron block and is fitted with an aluminum piston and chrome-plated rings.
- the electric motor is cradle-mounted so that the reaction torque can be measured by a strain arm.
- the engine is housed in a thermally insulated enclosure with an electric heater and is driven at 2000 rpm.
- test oil Prior to each test, the engine is flushed three times with 1-quart changes of test oil. During the test run, the engine and oil temperatures are increased continually from ambient until a 280° F. oil temperature is reached. The heat comes from engine friction, air compression work and from the electric heater. The engine and oil temperatures and the engine motoring torque are recorded continually during the test. A SEFT run takes about 4 hours. Each test oil evaluation is preceded by a run on a reference oil for a like period of time. The torque reference level for the engine shifts very slowly with time as a result of engine wear. Therefore, the test oil results are recorded compared to a reference band consisting of data from up to three reference runs made before and three runs made after the test oil evaluation.
- the present anti-friction additives also impart a dispersancy property to lubricating oil compositions.
- the reactants were charged and were blanketed with nitrogen.
- the reaction was heated to 160° C. removing water as it was formed and maintained at 160° C. for 8 hours.
- the product was filtered hot.
- the product had a TBN of 15.5 and contained 3.21 nitrogen.
- the test additive effected the greatest reduction of torque i.e., reduction in loss of energy due to friction. That is, the additive caused a reduction in loss of energy due to friction of more than 10 percent.
- the reactants were charged and blanketed with nitrogen and the reaction was heated to about 130° C. and maintained for 3 hours.
- the product was filtered hot.
- the product contained 3.47% nitrogen.
- the test additive effected the greatest reduction of torque i.e., reduction in loss of energy due to friction. That is, the additive caused a reduction in loss of energy due to friction of more than 12.0 percent.
Abstract
Description
TABLE III ______________________________________ Component Wt. % ______________________________________ Caprylic 8.0 Capric 7.0 Lauric 48.0 Myristic 17.5 Palmitic 8.2 Stearic 2.0 Oleic 6.0 Linoleic 2.5 ______________________________________
______________________________________ Reactant grams moles ______________________________________ Coconut Oil 164 0.25 Diethylenetriamine 34.8 0.338 Glycolic Acid, 70% Aq. Solution 37 0.35 Diluent Oil - 100 E Pale Stock HF 218 -- ______________________________________
TABLE IV ______________________________________ SMALL ENGINE FRICTION TEST Torque (Ft - Lbs) Run 1 2 3 4 5 6 Temperature (°F.) 130 160 190 220 250 280 ______________________________________ No Additive - 3.15 3.15 3.15 3.20 3.24 3.34 High (1) No Additive - 3.15 2.92 2.92 3.16 3.22 3.29 Low (2) No Additive - 3.15 3.04 3.04 3.18 3.23 3.32 Avg. Additive (3) 3.18 2.92 2.88 2.88 2.88 2.95 Torque -0.03 0.12 0.16 0.30 0.35 0.37 Reduction (4) ______________________________________ (1) Highest torque exhibited of lubricating oil containing no friction reducing additive. (2) Lowest torque exhibited of lubricating oil containing no friction reducing additive. (3) Torque exhibited by test additive containing lubricating oil. (4) Torque reduction provided by test additive in lubricating oil.
______________________________________ Reactant grams moles ______________________________________ Coconut Oil 164 0.25 Diethylenetriamine 34.8 0.338 Diluent Oil - 100 E Pale Stock HF 199 ______________________________________
TABLE V ______________________________________ SMALL ENGINE FRICTION TEST Torque (Ft - Lbs) Run 1 2 3 4 5 6 Temperature (°F.) 130 160 190 220 250 280 ______________________________________ No Additive - 3.1 3.01 3.01 3.20 3.24 3.30 High (1) No Additive - 3.1 2.95 2.95 3.11 3.20 3.26 Low (2) No Additive - 3.1 2.98 2.98 3.15 3.22 3.28 Avg. Additive (3) 3.1 2.90 2.85 2.85 2.87 2.88 Torque 0.0 0.08 0.13 0.30 0.35 0.40 Reduction (4) ______________________________________ (1) Highest torque exhibited of lubricating oil containing no friction reducing additive. (2) Lowest torque exhibited of lubricating oil containing no friction reducing additive. (3) Torque exhibited by test additive containing lubricating oil. (4) Torque reduction provided by test additive in lubricating oil.
Claims (17)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/766,469 US4647389A (en) | 1985-08-19 | 1985-08-19 | Anti-friction additives for lubricating oils |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/766,469 US4647389A (en) | 1985-08-19 | 1985-08-19 | Anti-friction additives for lubricating oils |
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US4647389A true US4647389A (en) | 1987-03-03 |
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US06/766,469 Expired - Lifetime US4647389A (en) | 1985-08-19 | 1985-08-19 | Anti-friction additives for lubricating oils |
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Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0349787A2 (en) * | 1988-06-08 | 1990-01-10 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | An additive to metal cold rolling oil |
US5474692A (en) * | 1992-08-03 | 1995-12-12 | Henkel Kommanditgesellschaft Auf Aktien | Lubricant concentrate and an aqueous lubricant solution based on fatty amines, a process for its production and its use |
DE19634605A1 (en) * | 1996-08-27 | 1998-03-05 | Schill & Seilacher | Use of polyhydroxycarboxamides as EP additives |
US6103674A (en) * | 1999-03-15 | 2000-08-15 | Uniroyal Chemical Company, Inc. | Oil-soluble molybdenum multifunctional friction modifier additives for lubricant compositions |
US20060046940A1 (en) * | 2004-08-27 | 2006-03-02 | Mohannad Almalki | Aqueous conveyor and cutting lubricant |
US20090312207A1 (en) * | 2005-10-11 | 2009-12-17 | Bartley Stuart L | Product of Amines with Hydroxy Acid as Friction Modifiers Suitable for Automatic Transmission Fluids |
US20100006049A1 (en) * | 2008-07-11 | 2010-01-14 | Basf Corporation | Composition and Method to Improve the Fuel Economy of Hydrocarbon Fueled Internal Combustion Engines |
US20100210490A1 (en) * | 2009-02-18 | 2010-08-19 | The Lubrizol Corporation | Amine Derivatives as Friction Modifiers in Lubricants |
JP2015021126A (en) * | 2013-07-18 | 2015-02-02 | アフトン・ケミカル・コーポレーションAfton Chemical Corporation | Amide alcohol friction modifiers for lubricating oils |
CN105154148A (en) * | 2015-08-25 | 2015-12-16 | 江西师范大学 | Preparation method of unsaturated fatty acid-estertype diesel antiwear agent |
US9909081B2 (en) | 2014-10-31 | 2018-03-06 | Basf Se | Alkoxylated amides, esters, and anti-wear agents in lubricant compositions |
WO2019167812A1 (en) * | 2018-02-28 | 2019-09-06 | 出光興産株式会社 | Lubricating oil composition |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3997469A (en) * | 1975-02-26 | 1976-12-14 | Nalco Chemical Company | Corrosion inhibition with oil soluble diamides |
US4512903A (en) * | 1983-06-23 | 1985-04-23 | Texaco Inc. | Lubricant compositions containing amides of hydroxy-substituted aliphatic acids and fatty amines |
-
1985
- 1985-08-19 US US06/766,469 patent/US4647389A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3997469A (en) * | 1975-02-26 | 1976-12-14 | Nalco Chemical Company | Corrosion inhibition with oil soluble diamides |
US4512903A (en) * | 1983-06-23 | 1985-04-23 | Texaco Inc. | Lubricant compositions containing amides of hydroxy-substituted aliphatic acids and fatty amines |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0349787A2 (en) * | 1988-06-08 | 1990-01-10 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | An additive to metal cold rolling oil |
EP0349787A3 (en) * | 1988-06-08 | 1990-04-18 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | An additive to metal cold rolling oil and a cold rolling oil composition containing the same |
US5474692A (en) * | 1992-08-03 | 1995-12-12 | Henkel Kommanditgesellschaft Auf Aktien | Lubricant concentrate and an aqueous lubricant solution based on fatty amines, a process for its production and its use |
DE19634605A1 (en) * | 1996-08-27 | 1998-03-05 | Schill & Seilacher | Use of polyhydroxycarboxamides as EP additives |
US5952274A (en) * | 1996-08-27 | 1999-09-14 | Schill & Seilacher Gmbh & Co. | Use of polyhydroxycarboxylamides as EP additives |
DE19634605B4 (en) * | 1996-08-27 | 2005-02-03 | Schill + Seilacher "Struktol" Ag | Use of sugar amides as EP additives and EP additives containing gluconic and / or glucoheptonic acid amides |
US6103674A (en) * | 1999-03-15 | 2000-08-15 | Uniroyal Chemical Company, Inc. | Oil-soluble molybdenum multifunctional friction modifier additives for lubricant compositions |
US20060046940A1 (en) * | 2004-08-27 | 2006-03-02 | Mohannad Almalki | Aqueous conveyor and cutting lubricant |
US20090312207A1 (en) * | 2005-10-11 | 2009-12-17 | Bartley Stuart L | Product of Amines with Hydroxy Acid as Friction Modifiers Suitable for Automatic Transmission Fluids |
US8148306B2 (en) | 2005-10-11 | 2012-04-03 | The Lubrizol Corporation | Product of amines with hydroxy acid as friction modifiers suitable for automatic transmission fluids |
US20100006049A1 (en) * | 2008-07-11 | 2010-01-14 | Basf Corporation | Composition and Method to Improve the Fuel Economy of Hydrocarbon Fueled Internal Combustion Engines |
US9447351B2 (en) | 2008-07-11 | 2016-09-20 | Basf Se | Composition and method to improve the fuel economy of hydrocarbon fueled internal combustion engines |
CN102395661A (en) * | 2009-02-18 | 2012-03-28 | 卢布里佐尔公司 | Amine derivatives as friction modifiers in lubricants |
CN102395661B (en) * | 2009-02-18 | 2017-03-15 | 路博润公司 | In the lubricant as the amine derivative of friction improver |
US8501674B2 (en) * | 2009-02-18 | 2013-08-06 | The Lubrizol Corporation | Amine derivatives as friction modifiers in lubricants |
KR20110131207A (en) * | 2009-02-18 | 2011-12-06 | 더루우브리졸코오포레이션 | Amine derivatives as friction modifiers in lubricants |
US20100210490A1 (en) * | 2009-02-18 | 2010-08-19 | The Lubrizol Corporation | Amine Derivatives as Friction Modifiers in Lubricants |
JP2015021126A (en) * | 2013-07-18 | 2015-02-02 | アフトン・ケミカル・コーポレーションAfton Chemical Corporation | Amide alcohol friction modifiers for lubricating oils |
US10246661B2 (en) | 2014-10-31 | 2019-04-02 | Basf Se | Alkoxylated amides, esters, and anti-wear agents in lubricant compositions and racing oil compositions |
US9909081B2 (en) | 2014-10-31 | 2018-03-06 | Basf Se | Alkoxylated amides, esters, and anti-wear agents in lubricant compositions |
US9920275B2 (en) | 2014-10-31 | 2018-03-20 | Basf Se | Alkoxylated amides, esters, and anti-wear agents in lubricant compositions and racing oil compositions |
CN105154148B (en) * | 2015-08-25 | 2018-05-18 | 江西师范大学 | A kind of preparation method of unsaturated fatty acid ester type diesel antiwear additive |
CN105154148A (en) * | 2015-08-25 | 2015-12-16 | 江西师范大学 | Preparation method of unsaturated fatty acid-estertype diesel antiwear agent |
WO2019167812A1 (en) * | 2018-02-28 | 2019-09-06 | 出光興産株式会社 | Lubricating oil composition |
JPWO2019167812A1 (en) * | 2018-02-28 | 2021-02-12 | 出光興産株式会社 | Lubricating oil composition |
US11168279B2 (en) | 2018-02-28 | 2021-11-09 | Idemitsu Kosan Co., Ltd. | Lubricating oil composition |
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